4-(Dimethylamino)Benzaldehyde → HCID 178482676, compound

HRID 416725Notes

Reaction equation

HRID 416725 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[CH3:28][N:29]([CH3:38])[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Cl:27][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])[CH2:13][CH2:12]2)=[C:7]2[N:8]=[C:34]([C:33]3[CH:36]=[CH:37][C:30]([N:29]([CH3:38])[CH3:28])=[CH:31][CH:32]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 46868214HCID 46868214, compound

Product 1

HCID 178482676HCID 178482676, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-phenylacetamide (0.040 g, 0.10 mmol), ethanol (3 ml), and 4-dimethylaminobenzaldehyde (0.019 g, 0.13 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.40 ml, 0.40 mmol). The reaction mixture was heated at 70° C. for 3 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% ethyl acetate in dichloromethane and then 1% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a yellow solid after trituration with diethyl ether (0.006 g, 12%); 1H-NMR (500 MHz, DMSO-d6) 2.76 (br s, 4H, piperazine N(CH2)2), 3.00 (s, 6H, N(CH3)2), 3.23 (s, 2H, NCH2CO), 3.75 (br s, 4H, piperazine N(CH2)2), 6.81 (d, J=7.90 Hz, 2H) and 8.01 (d, J=8.49 Hz, 2H) (3,5-C6H4NMe2 and 2,6-C6H4—NMe2), 7.07 (t, J=7.27 Hz, 1H, p-ArH), 7.32 (t, J=8.48 Hz, 2H, m-ArH), 7.67 (d, J=8.48 Hz, 2H, o-ArH), 8.06 (s, 1H, imidazo[4,5-b]pyridine 5-H), 9.77 (s, 1H, CONH), 13.11 (s, 1H, imidazo[4,5-b]pyridine N—H);

Workup

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-5b6f5fd396ff4fb09c49a9f383f1b58b
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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